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Record Information

Version

5.0

Status

Detected but not Quantified

Creation Date

2012-09-12 02:51:36 UTC

Update Date

2023-02-21 17:28:35 UTC

HMDB ID

HMDB0041194

Secondary Accession Numbers

HMDB41194

Metabolite Identification

Common Name

Methoxyeugenol

Description

Methoxyeugenol, also known as 4-allylsyringol, belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety. Methoxyeugenol is a sweet, bacon, and burnt tasting compound. Methoxyeugenol has been detected, but not quantified, in herbs and spices. This could make methoxyeugenol a potential biomarker for the consumption of these foods.

Structure

MOL 3D MOL SDF 3D SDF PDB 3D PDB SMILES InChI


  Mrv1652305271900202D          

 14 14  0  0  0  0            999 V2000
   15.1821  -14.7136    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1823  -13.8886    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.8980  -15.1298    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4678  -15.1254    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   15.8997  -13.4749    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   14.4665  -13.4724    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6123  -14.7179    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.9024  -15.9560    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
   16.6139  -13.8881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   13.7522  -13.8842    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   15.1851  -16.3695    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   17.3252  -13.4779    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.0376  -13.8881    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
   18.7503  -13.4732    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
  1  2  1  0  0  0  0
  1  3  2  0  0  0  0
  1  4  1  0  0  0  0
  2  5  2  0  0  0  0
  2  6  1  0  0  0  0
  3  7  1  0  0  0  0
  3  8  1  0  0  0  0
  5  9  1  0  0  0  0
  6 10  1  0  0  0  0
  8 11  1  0  0  0  0
  9 12  1  0  0  0  0
 12 13  1  0  0  0  0
 13 14  2  0  0  0  0
  7  9  2  0  0  0  0
M  END
> <DATABASE_ID>
HMDB0041194

> <DATABASE_NAME>
hmdb

> <SMILES>
COC1=CC(CC=C)=CC(OC)=C1O

> <INCHI_IDENTIFIER>
InChI=1S/C11H14O3/c1-4-5-8-6-9(13-2)11(12)10(7-8)14-3/h4,6-7,12H,1,5H2,2-3H3

> <INCHI_KEY>
FWMPKHMKIJDEMJ-UHFFFAOYSA-N

> <FORMULA>
C11H14O3

> <MOLECULAR_WEIGHT>
194.2271

> <EXACT_MASS>
194.094294314

> <JCHEM_ACCEPTOR_COUNT>
3

> <JCHEM_ATOM_COUNT>
28

> <JCHEM_AVERAGE_POLARIZABILITY>
20.53726426167309

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
1

> <JCHEM_IUPAC>
2,6-dimethoxy-4-(prop-2-en-1-yl)phenol

> <ALOGPS_LOGP>
2.23

> <JCHEM_LOGP>
2.4529086959999997

> <ALOGPS_LOGS>
-2.09

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
1

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA_STRONGEST_ACIDIC>
9.335852773119273

> <JCHEM_PKA_STRONGEST_BASIC>
-4.603104312142213

> <JCHEM_POLAR_SURFACE_AREA>
38.69

> <JCHEM_REFRACTIVITY>
55.25260000000001

> <JCHEM_ROTATABLE_BOND_COUNT>
4

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
1.59e+00 g/l

> <JCHEM_TRADITIONAL_IUPAC>
2,6-dimethoxy-4-(prop-2-en-1-yl)phenol

> <JCHEM_VEBER_RULE>
1

$$$$

HEADER    PROTEIN                                 27-MAY-19   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   27-MAY-19         0                                  
HETATM    1  C   UNK     0      28.340 -27.465   0.000  0.00  0.00           C+0
HETATM    2  C   UNK     0      28.340 -25.925   0.000  0.00  0.00           C+0
HETATM    3  C   UNK     0      29.676 -28.242   0.000  0.00  0.00           C+0
HETATM    4  O   UNK     0      27.007 -28.234   0.000  0.00  0.00           O+0
HETATM    5  C   UNK     0      29.679 -25.153   0.000  0.00  0.00           C+0
HETATM    6  O   UNK     0      27.004 -25.148   0.000  0.00  0.00           O+0
HETATM    7  C   UNK     0      31.010 -27.473   0.000  0.00  0.00           C+0
HETATM    8  O   UNK     0      29.684 -29.785   0.000  0.00  0.00           O+0
HETATM    9  C   UNK     0      31.013 -25.924   0.000  0.00  0.00           C+0
HETATM   10  C   UNK     0      25.671 -25.917   0.000  0.00  0.00           C+0
HETATM   11  C   UNK     0      28.346 -30.556   0.000  0.00  0.00           C+0
HETATM   12  C   UNK     0      32.340 -25.159   0.000  0.00  0.00           C+0
HETATM   13  C   UNK     0      33.670 -25.924   0.000  0.00  0.00           C+0
HETATM   14  C   UNK     0      35.001 -25.150   0.000  0.00  0.00           C+0
CONECT    1    2    3    4                                                  
CONECT    2    1    5    6                                                  
CONECT    3    1    7    8                                                  
CONECT    4    1                                                            
CONECT    5    2    9                                                       
CONECT    6    2   10                                                       
CONECT    7    3    9                                                       
CONECT    8    3   11                                                       
CONECT    9    5   12    7                                                  
CONECT   10    6                                                            
CONECT   11    8                                                            
CONECT   12    9   13                                                       
CONECT   13   12   14                                                       
CONECT   14   13                                                            
MASTER        0    0    0    0    0    0    0    0   14    0   28    0
END

COMPND    HMDB0041194
HETATM    1  C1  UNL     1       2.758  -0.343  -1.298  1.00  0.00           C  
HETATM    2  C2  UNL     1       3.122  -0.510  -0.044  1.00  0.00           C  
HETATM    3  C3  UNL     1       2.148  -0.449   1.059  1.00  0.00           C  
HETATM    4  C4  UNL     1       0.774  -0.192   0.617  1.00  0.00           C  
HETATM    5  C5  UNL     1       0.291   1.091   0.503  1.00  0.00           C  
HETATM    6  C6  UNL     1      -1.001   1.359   0.088  1.00  0.00           C  
HETATM    7  O1  UNL     1      -1.467   2.675  -0.020  1.00  0.00           O  
HETATM    8  C7  UNL     1      -0.643   3.771   0.288  1.00  0.00           C  
HETATM    9  C8  UNL     1      -1.813   0.280  -0.215  1.00  0.00           C  
HETATM   10  O2  UNL     1      -3.094   0.518  -0.627  1.00  0.00           O  
HETATM   11  C9  UNL     1      -1.351  -1.037  -0.109  1.00  0.00           C  
HETATM   12  O3  UNL     1      -2.222  -2.037  -0.428  1.00  0.00           O  
HETATM   13  C10 UNL     1      -1.973  -3.403  -0.393  1.00  0.00           C  
HETATM   14  C11 UNL     1      -0.058  -1.248   0.308  1.00  0.00           C  
HETATM   15  H1  UNL     1       1.713  -0.156  -1.526  1.00  0.00           H  
HETATM   16  H2  UNL     1       3.429  -0.377  -2.140  1.00  0.00           H  
HETATM   17  H3  UNL     1       4.161  -0.694   0.171  1.00  0.00           H  
HETATM   18  H4  UNL     1       2.158  -1.462   1.554  1.00  0.00           H  
HETATM   19  H5  UNL     1       2.462   0.337   1.802  1.00  0.00           H  
HETATM   20  H6  UNL     1       0.965   1.896   0.751  1.00  0.00           H  
HETATM   21  H7  UNL     1      -1.271   4.679   0.405  1.00  0.00           H  
HETATM   22  H8  UNL     1      -0.146   3.624   1.281  1.00  0.00           H  
HETATM   23  H9  UNL     1       0.129   3.950  -0.490  1.00  0.00           H  
HETATM   24  H10 UNL     1      -3.445   1.455  -0.710  1.00  0.00           H  
HETATM   25  H11 UNL     1      -0.922  -3.697  -0.492  1.00  0.00           H  
HETATM   26  H12 UNL     1      -2.454  -3.834   0.529  1.00  0.00           H  
HETATM   27  H13 UNL     1      -2.514  -3.913  -1.242  1.00  0.00           H  
HETATM   28  H14 UNL     1       0.264  -2.284   0.378  1.00  0.00           H  
CONECT    1    2    2   15   16
CONECT    2    3   17
CONECT    3    4   18   19
CONECT    4    5    5   14
CONECT    5    6   20
CONECT    6    7    9    9
CONECT    7    8
CONECT    8   21   22   23
CONECT    9   10   11
CONECT   10   24
CONECT   11   12   14   14
CONECT   12   13
CONECT   13   25   26   27
CONECT   14   28
END

View in JSmol View Stereo Labels

Synonyms

Value	Source
2,6-Dimethoxy-4-(2-propenyl)-phenol	HMDB
2,6-Dimethoxy-4-(2-propenyl)phenol, 9ci	HMDB
2,6-Dimethoxy-4-allylphenol	HMDB, MeSH
2,6-Dimethoxychavicol	HMDB
4-(2-Propenyl)-2,6-dimethoxyphenol	HMDB
4-Allyl-2,6-dimethoxy-phenol	HMDB
4-Allyl-2,6-dimethoxyphenol	HMDB
4-Allyl-2,6-dimethoxyphenol, 8ci	HMDB
4-Allyl-2,6-dimetoxyphenol	HMDB
4-Allylsyringol	HMDB, MeSH
4-Hydroxy-3,5-dimethoxyallylbenzene	HMDB, MeSH
N-Allylcyclohexylamine	HMDB
Phenol, 2,6-dimethoxy-4-(2-propenyl)- (9ci)	HMDB
Phenol, 4-(2-propenyl)-2,6-dimethoxy	HMDB
Phenol, 4-allyl-2,6-dimethoxy- (8ci)	HMDB
2,6-Dimethoxy-4-(2-propenyl)phenol	MeSH
6-Methoxyeugenol	MeSH

Chemical Formula

C₁₁H₁₄O₃

Average Molecular Weight

194.2271

Monoisotopic Molecular Weight

194.094294314

IUPAC Name

2,6-dimethoxy-4-(prop-2-en-1-yl)phenol

Traditional Name

2,6-dimethoxy-4-(prop-2-en-1-yl)phenol

CAS Registry Number

6627-88-9

SMILES

COC1=CC(CC=C)=CC(OC)=C1O

InChI Identifier

InChI=1S/C11H14O3/c1-4-5-8-6-9(13-2)11(12)10(7-8)14-3/h4,6-7,12H,1,5H2,2-3H3

InChI Key

FWMPKHMKIJDEMJ-UHFFFAOYSA-N

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as methoxyphenols. Methoxyphenols are compounds containing a methoxy group attached to the benzene ring of a phenol moiety.

Kingdom

Super Class

Class

Sub Class

Direct Parent

Alternative Parents

Substituents

M-dimethoxybenzene
Dimethoxybenzene
Methoxyphenol
Phenoxy compound
Methoxybenzene
Phenol ether
Anisole
Alkyl aryl ether
Monocyclic benzene moiety
Ether
Organic oxygen compound
Hydrocarbon derivative
Organooxygen compound
Aromatic homomonocyclic compound

Molecular Framework

Aromatic homomonocyclic compounds

External Descriptors

phenols (CHEBI:86562 )
phenylpropanoid (CHEBI:86562 )
dimethoxybenzene (CHEBI:86562 )

Ontology

Sweet

Disposition

Biological location

Cellular substructure

Extracellular (HMDB: HMDB0041194)
Cytoplasm (HMDB: HMDB0041194)

Non-excretory biofluid

Biofluid or Excreta

Blood (PMID: 32966057)

Excreta

Biofluid or Excreta

Urine (PMID: 32966057)

Route of exposure

Enteral

Ingestion (HMDB: HMDB0041194)

Source

Exogenous

Food

Food (HMDB: HMDB0041194)

Fruit

Tropical fruit

Banana (FooDB: FOOD00208)

Herb and spice

Spice

Star anise (FooDB: FOOD00090)

Herbs and Spices (FooDB: FOOD00866)

Endogenous

Plant

Plant (HMDB: HMDB0041194)

Process

Not Available

Role

Biological role

Nutrient (HMDB: HMDB0041194)

Physical Properties

State

Not Available

Experimental Molecular Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	168.00 to 169.00 °C. @ 11.00 mm Hg	The Good Scents Company Information System
Water Solubility	307.4 mg/L @ 25 °C (est)	The Good Scents Company Information System
LogP	2.338 (est)	The Good Scents Company Information System

Experimental Chromatographic Properties

Not Available

Predicted Molecular Properties

Property	Value	Source
Water Solubility	1.59 g/L	ALOGPS
logP	2.23	ALOGPS
logP	2.45	ChemAxon
logS	-2.1	ALOGPS
pKa (Strongest Acidic)	9.34	ChemAxon
pKa (Strongest Basic)	-4.6	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	3	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	38.69 Å²	ChemAxon
Rotatable Bond Count	4	ChemAxon
Refractivity	55.25 m³·mol⁻¹	ChemAxon
Polarizability	20.54 Å³	ChemAxon
Number of Rings	1	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	Yes	ChemAxon
MDDR-like Rule	No	ChemAxon

Predicted Chromatographic Properties

Predicted Collision Cross Sections

Predictor	Adduct Type	CCS Value (Å²)	Reference
DarkChem	[M+H]+	145.185	31661259
DarkChem	[M-H]-	144.024	31661259
DeepCCS	[M+H]+	142.898	30932474
DeepCCS	[M-H]-	140.449	30932474
DeepCCS	[M-2H]-	176.039	30932474
DeepCCS	[M+Na]+	151.486	30932474
AllCCS	[M+H]+	142.3	32859911
AllCCS	[M+H-H2O]+	138.1	32859911
AllCCS	[M+NH4]+	146.2	32859911
AllCCS	[M+Na]+	147.4	32859911
AllCCS	[M-H]-	142.2	32859911
AllCCS	[M+Na-2H]-	142.9	32859911
AllCCS	[M+HCOO]-	143.7	32859911

Predicted Kovats Retention Indices

Underivatized

Metabolite	SMILES	Kovats RI Value	Column Type	Reference
Methoxyeugenol	COC1=CC(CC=C)=CC(OC)=C1O	2568.4	Standard polar	33892256
Methoxyeugenol	COC1=CC(CC=C)=CC(OC)=C1O	1559.2	Standard non polar	33892256
Methoxyeugenol	COC1=CC(CC=C)=CC(OC)=C1O	1609.5	Semi standard non polar	33892256

Derivatized

Derivative Name / Structure	SMILES	Kovats RI Value	Column Type	Reference
Methoxyeugenol,1TMS,isomer #1	C=CCC1=CC(OC)=C(O[Si](C)(C)C)C(OC)=C1	1606.1	Semi standard non polar	33892256
Methoxyeugenol,1TBDMS,isomer #1	C=CCC1=CC(OC)=C(O[Si](C)(C)C(C)(C)C)C(OC)=C1	1849.0	Semi standard non polar	33892256

Spectra

GC-MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted GC-MS	Predicted GC-MS Spectrum - Methoxyeugenol GC-MS (Non-derivatized) - 70eV, Positive	splash10-0fvl-1900000000-6bb088a84e5d530fd6a9	2016-09-22	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methoxyeugenol GC-MS (1 TMS) - 70eV, Positive	splash10-0umi-6290000000-ddd8fa9b2271b5e885fa	2017-10-06	Wishart Lab	View Spectrum
Predicted GC-MS	Predicted GC-MS Spectrum - Methoxyeugenol GC-MS (Non-derivatized) - 70eV, Positive	Not Available	2021-10-12	Wishart Lab	View Spectrum

MS/MS Spectra

Spectrum Type	Description	Splash Key	Deposition Date	Source	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methoxyeugenol 10V, Positive-QTOF	splash10-0002-0900000000-bf95219cde86264ddd0e	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methoxyeugenol 20V, Positive-QTOF	splash10-0002-1900000000-b3789d49cb1d02ff5e01	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methoxyeugenol 40V, Positive-QTOF	splash10-0006-7900000000-2b4993fb9c656f50c42f	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methoxyeugenol 10V, Negative-QTOF	splash10-0006-0900000000-1cb6aa76e853c97dffa4	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methoxyeugenol 20V, Negative-QTOF	splash10-0006-0900000000-7a91ae9052ae5aad302c	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methoxyeugenol 40V, Negative-QTOF	splash10-0a6s-3900000000-2d0b6fcc14c0098a2b40	2016-08-03	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methoxyeugenol 10V, Positive-QTOF	splash10-0002-0900000000-62e0a52145f670b429c1	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methoxyeugenol 20V, Positive-QTOF	splash10-0002-1900000000-9d68b2e71ed843fa1b9a	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methoxyeugenol 40V, Positive-QTOF	splash10-00ou-9100000000-2bed599e076c0fa0e319	2021-09-23	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methoxyeugenol 10V, Negative-QTOF	splash10-0006-0900000000-b336d2e98c182ff7e0b0	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methoxyeugenol 20V, Negative-QTOF	splash10-01ox-1900000000-fb6a83b5e663fc04cc80	2021-09-24	Wishart Lab	View Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - Methoxyeugenol 40V, Negative-QTOF	splash10-02t9-9300000000-a8dc328f94fd3fc6319f	2021-09-24	Wishart Lab	View Spectrum

NMR Spectra

Spectrum Type	Description	Deposition Date	Source	View

IR Spectra

Spectrum Type	Description	Deposition Date	Source	View
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M-H]-)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+H]+)	2023-02-04	FELIX lab	View Spectrum
Predicted IR Spectrum	IR Ion Spectrum (Predicted IRIS Spectrum, Adduct: [M+Na]+)	2023-02-04	FELIX lab	View Spectrum

Biological Properties

Cellular Locations

Cytoplasm
Extracellular

Biospecimen Locations

Blood
Urine

Tissue Locations

Not Available

Pathways

Not Available

Name	SMPDB/PathBank	KEGG

Normal Concentrations

Biospecimen	Status	Value	Age	Sex	Condition	Reference	Details
Blood	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details
Urine	Detected but not Quantified	Not Quantified	Adult (>18 years old)	Both	Normal	32966057	details

Abnormal Concentrations

Not Available

Associated Disorders and Diseases

Disease References

None

Associated OMIM IDs

None

External Links

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FooDB ID

FDB021092

KNApSAcK ID

C00055253

Chemspider ID

196968

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

226486

PDB ID

Not Available

ChEBI ID

86562

Food Biomarker Ontology

Not Available

VMH ID

Not Available

MarkerDB ID

Not Available

Good Scents ID

rw1037281

References

Synthesis Reference

Not Available

Material Safety Data Sheet (MSDS)

Not Available

General References

(). Yannai, Shmuel. (2004) Dictionary of food compounds with CD-ROM: Additives, flavors, and ingredients. Boca Raton: Chapman & Hall/CRC.. .

Showing metabocard for Methoxyeugenol (HMDB0041194)

MOL for HMDB0041194 (Methoxyeugenol)

3D MOL for HMDB0041194 (Methoxyeugenol)

3D SDF for HMDB0041194 (Methoxyeugenol)

3D-SDF for HMDB0041194 (Methoxyeugenol)

PDB for HMDB0041194 (Methoxyeugenol)

3D PDB for HMDB0041194 (Methoxyeugenol)

SMILES for HMDB0041194 (Methoxyeugenol)

INCHI for HMDB0041194 (Methoxyeugenol)

Structure for HMDB0041194 (Methoxyeugenol)

3D Structure for HMDB0041194 (Methoxyeugenol)

Predicted Collision Cross Sections

Predicted Kovats Retention Indices

Underivatized

Derivatized

GC-MS Spectra

MS/MS Spectra

NMR Spectra

IR Spectra